MANGANESE(III)-MEDIATED RADICAL ADDITIONS OF DIMETHYL MALONATE TO OLEFINS - THE CHEMOSELECTIVE SYNTHESIS OF DIESTERS AND LACTONES

Authors
LINKER T KERSTEN B LINKER U PETERS K PETERS EM VONSCHNERING HG
Citation
T. Linker et al., MANGANESE(III)-MEDIATED RADICAL ADDITIONS OF DIMETHYL MALONATE TO OLEFINS - THE CHEMOSELECTIVE SYNTHESIS OF DIESTERS AND LACTONES, Synlett, (5), 1996, pp. 468
Citations number
32
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Synlett → ACNP
ISSN journal
09365214
Issue
5
Year of publication
1996
Database
ISI
SICI code
0936-5214(1996):5<468:MRAODM>2.0.ZU;2-9
Abstract
The radical addition of dimethyl malonate (1) to alkyl-substituted ole fins 2a-d can be mediated by potassium permanganate and allows the che moselective synthesis of saturated esters 4a-d. A high degree of stere oselectivity is observed with 1,5-cyclooctadiene (2d) and trans-stilbe ne (2f). In the presence of Mn(OAc)(3) the lactone 6f is obtained in d iastereomerically pure form in 86% yield.